Thionyl Chloride → Ethyl 6-(chloromethyl)nicotinate

HRID 1030513ノート

反応式

HRID 1030513 の反応式
O[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:16][CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]=1

参加物

5

反応物 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 15045504Ethyl 6-(hydroxymethyl)pyridine-3-carboxylate

生成物 1

HCID 15045505Ethyl 6-(chloromethyl)nicotinate収率 90.9%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

A solution of 10.5 g of ethyl 6-hydroxymethylnicotinate in chloroform (100 ml) was cooled to 0° C., and 8.28 g of thionyl chloride was added dropwise to the solution. The mixture was stirred at 0° C. for 2 hours, an aqueous solution of sodium hydrogencarbonate was added, and the mixture was extracted with dichloromethane. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1) to obtain 10.52 g of ethyl 6-chloromethylnicotinate.

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexene/ethyl acetate=6/1)

出典と根拠

ORDレコード
ord-c261d04a19c4419686e6e6b2aa1e8fca
出典データセット
uspto-grants-1992_04
特許番号
US05106859

反応ノート

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